How I get dressed in the morning

Everyone gets dressed in the morning. Most put no thought into it; a few put too much into it.

My approach, formed through nothing more than hazard and habit, is to do one of two things:

Pick out one piece that I really want to wear (usually something new, often something unusual) or

Pick out an outfit I already know I like, and fiddle around the margins

With the outfit shown here in Milan, for example, I wanted to wear my royal-blue flannel DB suit from Anderson & Sheppard. Because it’s still one of the most beautiful things I own, and it’s not really office attire.

Only dark-brown shoes really go with it: black or tan create too much contrast, when it needs the opposite. So I picked by Edward Green Top Drawer monk-straps.

Equally, a white shirt can work, but blue is much better for reducing that contrast, so a plain spread-collar shirt from Luca Avitabile.

Now the tricky bits – the tie and the handkerchief.

Soft, autumnal colours achieve something similar to the softening of the brown shoes and blue shirt, so I considered browns, oranges and greens, before selecting this seven-fold untipped tie from EG Cappelli in a burnt orange.

Helpfully the tie has a blue geometric device in the print, which makes it a little easier to sit with the blue of the suit.

For the pocket square, again I considered several muted colours – including muted variations on white linen – before selecting a Drake’s silk/wool handkerchief in green and navy.

Given the cold, wet day in Milan, a scarf was also a very useful thing to have in my briefcase, and grey is a very versatile option. Other colours as mentioned above, such as browns, would also have worked, though might have risked a clash of too much colour.

The alternative dressing approach is to pick out an outfit I already know and like, and then give it a touch of originality.

It’s hard to keep all these outfits in my head. Most of them are scattered over the past nine years of this website, but I do have a folder with them all in to scan through when I’m drawing a blank.

In order to retain the same approach, but avoid wearing exactly the same thing, I have worn it recently with a navy Friday Polo and my Solito navy-cashmere jacket. And I have worn a paler grey shirt and chalky navy tie.

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Great post! I assume it varies massively, but what is your normal progression in terms of elements in an outfit? E.g. Suit, shirt, tie, shoes, socks, pocket squares. Interesting for someone who wants to avoid repetition of outfits.

Love these posts! As with Adam a look book of outfits (i.e. a curated re-visitation of the archive) would be a great, and helpful, book. FYI the website Looktastic, under How to Wear/brown jackets, has the Pitti shot of you. A couple of related questions. I have a similar cord suit (SB) but find it difficult to make it come to life due to the shade and older cut, how might this be achieved? Also, re. wardrobe management, you’ve mentioned you store out non-season wear. Facing a similar problem can I ask how you store; storage bags, garment rail etc.?

I work in a law firm, where most of the people wear suits without tie. I only wear suits with a tie, so I also wear grey pants and sports coats. The sports coats I have are dark green tweed, dark blue cashmere, dark brown hopsack and double breasted unstructured blue light weight wool. What would you recommend to buy next that I could wear 3-4 seasons? It has to be fairly formal… If you have more than one tip, I appreciate that too!! Keep up the good work.

Love the suit. I have a couple of bespoke suits from GB. Both are single breasted. I’m thinking of a navy db for my next one but am concerned it might be too formal. Would you recommend getting another single breasted for versatility?

Hi Simon,
I think most PS readers if not all share your taste. I find this one very chic. Strangely enough, in my case before going to bed, I already have my outfit in my head, so to speak. And usually in the morning I help instead my girlfriend choose hers.
John

Hi Simon, it’s the unwashed Kishorn, right? Did yours also fluff initially, fairly visible on a darker background like that blue flannel? Does it get less with time? I much love the fabric and just wonder what to expect from here.. thanks.

To organize my clothing I use the Stylebook app for men on my iPhone. I took photos of every piece of clothing, and organized them into outfits inside the app. I can then assign them to a day in the calendar. It’s especially helpful when planning what to pack for a trip.

Thanks.
Unfortunately, I don’t think this flannel is available any more. Mills change their collections every season to some extent (too often in my view) and as a result, unusual materials are not available for that long. It was a Lesser flannel in royal blue. There are similar things out there, but worth going into your tailor and asking him what he would suggest in the same area.

Hi Simon.
Although I think white shirts can look great with light coloured suits I am beginning to develop a phobia of wearing them with dark coloured suits. I see that you tend to wear more blue shirts than any other colour. Do you find blue to be the most harmonious of shirt colours?
Many thanks

With regards to the Begg & Co scarf, do you recall which specific scarf it is? Based on the other comment I thought perhaps one of their silver grey but the fringe does not match that of the photograph.

Do you think this jacket would work as a separate, perhaps with mid or pale grey trousers?

I’ve wanted to commission a royal blue flannel DB ever since I saw one dressed beautifully in the window of Hackett a couple of years ago, but have never quite been able to justify it on grounds of versatility. Not quite business attire, not quite smart-casual. Kind of suitable formality for a summer wedding, without actually being suitable for summer (being flannel). Wearing part of the suit as a jacket might help me justify it a little more to myself….